Dimethylformamide → 3H-Imidazo[4,5-c]pyridine-7-carbonitrile

HRID 2409027Notes

Reaction equation

HRID 2409027 reaction equation
Br[C:2]1[C:3]2[NH:10][CH:9]=[N:8][C:4]=2[CH:5]=[N:6][CH:7]=1.[NH4+].[OH-].[CH3:13][N:14](C=O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C-]#N.[C-]#N.[Zn+2]>[N:10]1[C:3]2[C:2]([C:13]#[N:14])=[CH:7][N:6]=[CH:5][C:4]=2[NH:8][CH:9]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 178419455HCID 178419455, compound

Product 1

HCID 705571723H-Imidazo[4,5-c]pyridine-7-carbonitrileYield 67%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

To a solution of 7-bromo-1H-imidazo[4,5-c]pyridine (3 g, 15.6 mmol) in DMF (10 mL) was added Pd(PPh3)4 (1.0 g) and Zn(CN)2 (1.2 g, 10 mmol). The reaction mixture was irradiated in a microwave at 100° C. for 2 h under Ar. The reaction mixture was poured into aqueous NH4OH and extracted with DCM. The organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography to afford 1.5 g (67%) of 3H-imidazo[4,5-c]pyridine-7-carbonitrile as a white solid; MS (ESI)/v/z: 145.0 [M+1]+.

Workup

  1. customThe reaction mixture was irradiated in a microwave at 100° C. for 2 h under Ar
  2. extractionextracted with DCM
  3. dry with materialThe organic extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by SiO2 chromatography

Sources & evidence

ORD record
ord-e0b482a1005b465b88aeba75d68f5a5e
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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